p-Toluenesulfonic acid → N-(2,6-difluorophenyl)-3-(3-{2-[(5-methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)benzamide (Intermediate Example 1) (0.050 g, 0.11 mmol), 5-methyl-2-(methyloxy)-4-{4-[4-(methylsulfonyl)-1-piperazinyl]-1-piperidinyl}aniline (Example 236, Step B) (0.041 g, 0.11 mmol) and para-toluenesulfonic acid (0.049 g, 0.26 mmol) in i-PrOH (5 mL) was heated in a microwave at 175° C. for 20 min. The reaction mixture was concentrated onto silica gel and purified by flash chromatography to afford the title compound (0.031 g, 35%). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.24 (s, 1H), 9.42 (br. s., 1H), 8.48 (s, 1H), 8.34 (s, 1H), 8.25 (d, J=5.1 Hz, 1H), 8.06 (d, J=8.1 Hz, 1H), 7.83 (d, J=7.8 Hz, 1H), 7.75 (d, J=8.9 Hz, 1H), 7.62 (t, J=7.7 Hz, 1H), 7.34-7.55 (m, 3H), 7.17-7.29 (m, 2H), 6.95-7.06 (m, 1H), 6.77 (s, 1H), 6.51 (d, J=5.2 Hz, 1H), 3.80 (s, 3H), 3.05-3.17 (m, 6H), 2.88 (s, 3H), 2.59-2.73 (m, 6H), 2.38-2.46 (m, 1H), 2.16 (s, 3H), 1.81-1.90 (m, 2H), 1.53-1.68 (m, 2H). MS (M−H, ES−) 806.

Provenance & Evidence